My Sister's Boyfriend

At 23, my sister was 6 years older than me and she never let me forget it for a second! All my life, id been given her second hand stuff... clothes, shoes, school books etc. All my teachers at school compared me to her, my parents, all my family! I was never ever good enough, she was always better at everything or had done it before me.

She teased me relentlessly about everything, my hair, my body, my style - everything!

The only thing I had that she didn't was breasts. Hers never really came in, they blossomed to a B-cup and nothing more. Mine, on the other hand, were generous DD's. She was jealous and always had been.

I was finally growing out of her shadow and becoming my own person, not just 'Molly's sister'.

Her boyfriend, Sam, had always treated me well. He hadn't been around long but he always stopped and chatted with me when he came over. He was tall with short, dark hair and big, broad shoulders. He had just graduated from university, as had my sister.

I loved to flirt with him, it drove Molly crazy when he claimed he was just being nice to me. That summer, I set my sights on him, determined to make him mine.

After a few weeks of harmless flirting I decided it was time to step things up a little bit. Molly got a job and worked 5 days a week now. Early one morning, I took her phone and hid it, not wanting to be late, she left without it and went to work. Mom and dad left a while later and once again, I was home alone.

I texted Sam from Molly's phone.

"Couldn't wait to see you, taking today off, want to come over?"

He replied a while later

"Sure, I'll come by in about an hour?"

"Perfect, see you then." I replied.

I smiled to myself at the thought of his face as I answer the instead of Molly.

I started getting ready, filing through my wardrobe, trying to decide what to wear... simple and casual, shy and sweet or a little bit slutty?

Eventually, I decided on a mix of shy, sweet and slutty - A cute pink skirt (that used to be molly's) and a white vest top. I opted for no panties and no bra, a nice surprise for Sam, hopefully. I put on a little bit of makeup and brushed my hair, leaving it in soft curls, down my back.

I had shaved my legs and tidied up 'down there' earlier, keeping a small patch of dark, wry hair on my soft mound.

I went downstairs, got myself a drink and perched nervously on the couch waiting for Sam's arrival. The knock at the door made me jump, I took a deep breath and got up to answer it, adjusting my skirt as I went.

I opened the door with a big smile and greeted the handsome man standing in front of me. He smiled, looking a little puzzled.

"Hey Chloe, uh... is Molly in?" he asked, as he walked in.

I tried to keep a serious face "Um, no shes at work actually." I replied.

"Oh, right." Confusion swept over his face again "She text me saying she was home."

"Haha, weird!" I giggled nervously "Can I get you something to drink?" I squeaked.

"Sure, I'll have a bottle of water, please."

He followed me into the kitchen as I went to get some water.

"So what are you doing today?" he asked.

I grabbed a bottle out of the fridge and handed it to him

"Oh, not much, just chilling today." I smiled.

I could feel his eyes on my body, looking me over.

"Cool." He mumbled. "Do you know what time Molly gets back? Maybe I should text her again."

"No!" I exclaimed, a little too forcefully.

He looked at me, taken aback slightly

"...Why not?" he asked

"Well, its just, she's at work and probably super busy, she doesn't usually finish until 6 on Wednesdays." I recovered quickly.

"I'll just shoot her a quick text and she'll see it on her break." He said as he pulled out his phone and began composing the message.

He sent it before I had time to convince him otherwise and almost instantaneously, Molly's phone beeped from the couch where I left it

"Is that...? That sounded a lot like Molly's phone..." he commented, a little disconcerted. He looked at me and I started to blush.

I panicked and ran infront of him as he headed for the couch

"Wait!" I squeaked. "I have a confession to make!" I put my hands on his chest, in an attempt to stop him, and felt my body tingle with excitement.

"I took Molly's phone and texted you this morning."

"You what? Why?" he asked, the puzzled look returned to his face.

"I...I just wanted to see you... I was bored I guess." I mumbled, my hands falling from his chest, my cheeks burning.

He walked over to the couch and picked up mollys phone.

"Why didn't you just text me from your phone?" he quizzed me.

"I didn't think you'd come." I muttered, sitting down on the couch

He sat next to me, laughing.

"Why not? I like spending time with you."

"Really? But Molly doesn't like it when I hang around you" I replied.

"But I like it" He smiled at me, "And Molly's not here."

I looked up and smiled at him, his dark features even more gorgeous close up.

He moved his hand to my bare leg and squeezed a little.

A shiver ran down my spine as he touched my skin. I could feel my nipples harden beneath my thin shirt.

His eyes glanced down at the hard peaks, clearly visible, stretching the already see-through material. I bit my lip.

"Oops." I giggled, a bit embarrassed.

I could feel his intense gaze on me and I looked into his striking blue eyes as he inched his hand further up my leg and I made no attempt to stop him.

"Chloe..." He moaned quietly. "We shouldn't..." He began to protest.

"Shhhh." I hushed him. I didn't want him to stop. I spread my legs a little wider, encouraging him to keep going.

He pulled his hand away. "We shouldn't do this." He sighed.

"Why? You want it, I want it!" I tried to persuade him, moving closer. "Don't you?" I asked, biting my lip again.

"Don't do that, Chloe, it drives me crazy." He moaned, exasperated.

"Sorry." I mumbled, biting my lip subconsciously.

He grabbed me and pulled me onto his lap, he looked at me for a second and I moved in to kiss him.

He pulled me closer, his tongue parting my lips and exploring my mouth.

I straddled him on the couch, kissing him deeper.

Id never felt like this, it was so wrong but so right, and knowing that my sister would kill me for it made it so much more exciting.

His hands quickly found their way under my top and began fondling my perky, round breasts.

I started to moan, quietly at first, as he tweaked and teased my nipples, rolling them between his fingers, tugging them and pinching them. It felt amazing. I could feel my pussy tingling, getting wetter by the second as he teased me.

Before long, his hands were working his way down my body, feeling down my hips and to my legs before sliding up my skirt.

He started to massage my ass, but pulled away from our kiss.

"You're not wearing any panties..." he remarked with a smirk.

"Or a bra." I said, winking as I peeled my top off, releasing my bouncy tits.

He grabbed and squeezed my ass hard and I resumed kissing him.

He started to kiss my neck, still squeezing and rubbing my ass.

"I think we should take this upstairs." I moaned breathlessly.

Wordlessly, he picked me up. I wrapped my arms around his neck and clamped my legs around him as he held my ass to support me.

He carried me up the stairs and threw me down on the bed... Molly's bed.

"Thought you might get a kick out of this." He grinned.

I wriggled out of my skirt and watched him undress to nothing but his boxer shorts. He threw his clothes in a pile on the floor and crawled between my legs.

He pulled himself up to kiss me again, starting to make his way down my body again, kissing my neck and shoulders, moving swiftly to my bare breasts. He had one in his hand and the other he was teasing with his mouth. I started to moan and squirm as he pinched and pulled at my hard nipple with his fingers, biting the other softly.

"Fuckkk!" I moaned, loudly.

He continued playing with me for a while, before progressing downwards. He kissed down my stomach and legs, pausing to admire my glistening slit.

He kissed my inner thighs and bit them lightly. The anticipation grew as he built up to what he was going to do next.

"Please..." I whispered, breathing heavily. "Please, Sam."

He looked up at me, a naughty glint in his eyes as I begged him to pleasure me.

He pushed my legs further apart and finally, buried his tongue in my wet slit. He licked up and down, flicking his tongue over my clit, tasting me, teasing me.

I grabbed handfuls of his hair, pushing him closer to me, his tongue sweeping over every inch of my pussy.

"Don't stop!" I cried out, close to cumming as he worked me over with his tongue.

He lapped at me, harder and faster now, ready for me to cum. My moans got louder and louder as he brought me closer.

Suddenly, he stopped. My moans came to an abrupt pause.

"You're not cumming yet." He announced with a wicked grin.

I scowled at him, visibly disappointed.

"Get up." He ordered.

I clambered out of bed as he stepped out of his boxers. My eyes widened in surprised as I got my first glance of his cock.

The first thing I noticed was the girth. It was so thick. He was average length, but my god, did he make up for it in girth.

"I want you to cum on my cock." He grabbed me and pulled me back on to the bed, on top of him.

"It's easier this way" he said "It wont hurt as much."

I gulped as I climbed on top of him and hovered over his massively thick cock.

I took a deep breath and slowly lowered myself on to him. I felt it stretch the opening of my pussy. I cried out as I tried to push it in further. I could feel it stretching my tight little pussy as I lowered myself further. I kept going until it was all inside me and I was sitting on him.

"I'm impressed." He remarked, his hands feeling up my body again.

The burning pain had subsided and I was adjusting to this feeling of complete fullness.

"It's so thick!" I moaned, shuffling slightly.

I raised up slightly, feeling his cock move inside me. Fuck, it felt so good.

He closed his eyes and let out a quiet moan as I began to move little by little.

I started to bounce more vigorously now, accustomed to the feeling of him inside me, stretching me.

He grabbed my hips and pushed me down hard on his cock each time. I was close again, I could feel it building up inside me. My hand reached down to my clit and started massaging it, edging closer and closer.

He grabbed my hips and slammed me down harder and harder on to his cock.

I let out a loud moan and came hard, shaking and moaning as he pounded me.

I kept bouncing, recovering slightly from my orgasm before climbing off Sam.

I repositioned myself, my pussy inches from his face, and took his dripping cock in my mouth. I sucked it clean, licking every last drop of my juices off his throbbing member. I felt his tongue between my legs again, lapping at my pussy while I devoured his cock.

When he finished eating me out, he pushed me forwards a little, signaling me to get up. I moved and he got behind me, moving the tip of his cock to my slit.

He grabbed a handful of my hair and pulled it back, holding me in place before plunging deep into me.

"You fuck much better than your sister" He snarled in my ear.

I practically came on the spot, moaning and shaking as I orgasmed on his cock.

He began to pump me harder, moving a hand to my ass, squeezing it and grabbing it. I felt his thumb on my tight asshole, massaging it, pushing a little harder with every revolution.

It felt amazing! I've never had anyone touch me like that before and I wanted more.

"Harder!" I cried, breathlessly.

He started slamming into me even harder and suddenly jammed his thumb into my asshole.

I gasped, a little shocked at the feeling before a quiet "Fuck yesss." Escaped my lips.

He started to move his thumb inside me and I could feel myself building up to climax again.

"You like that, slut?" he asked between thrusts.

"Yes!" I moaned "Feels so fucking good."

He laughed a little before withdrawing his thumb and his cock from my throbbing pussy.

I felt his thick member pressing against my asshole.

"Are you gonna let me fuck your pretty little ass, Chloe?"

I turned my head to look at him and nodded shyly.

"I've never done anal before..." I commented, biting my lip.

"Don't worry, you're gonna love it." He said with a wicked smile on his face.

He leaned down and and licked my tight little hole, swirling his tongue around it before letting a big glob of spit fall out of his mouth and onto my ass.

"Ready?" he asked, his cock resting on my ass.

"Yeah..." I whispered, bracing myself.

He spread my ass cheeks and pushed his cock against me.

I yelped as he entered my ass, stretching it over his thick, wet cock. The burning sensation spreading as he pushed deeper into me. He kept pushing until he bottomed out, his prick entirely inside my ass.

I let out a loud sigh, adjusting to this odd feeling of fullness as he started to move in and out of my ass.

At first the friction was a little painful, but soon it turned into pleasure and my hand found my clit while Sam impaled my ass.

I started massaging my clit, my pussy still dripping wet. Sam's thrusts got faster as he dragged his cock out of me and forced it back in, over and over. I was ready to cum again and I cried out, drenching my fingers again.

"Fuck Chloe!" he grunted "Your ass is perfection, I'm gonna cum..."

He started moaning and grunting as he approached orgasm. He clutched my hips and pumped his hot, sticky seed into my tight, virgin ass.

"Fuck" he murmured as he finished shooting his load in my ass.

He stopped and pulled out of me slowly. I slumped down on the bed, completely spent.

He stood up, his cock drooping slightly and sat on the bed next to me.

I could feel the hot liquid leaking out of my ass, dripping down to my pussy.

"That was amazing." He grinned at me.

"I know." I agreed, smiling. "No ones ever fucked my ass, it was fantastic."

He laid down next to me and smacked my ass playfully, more ejaculate oozing out of me.

"I think we should do this more often." He smirked. "What do you think?"

"Definitely!" I giggled. "If I knew you were this great in bed, I would've seduced you ages ago."

"It'll be our little secret; Molly never has to know."

Keeping it a secret from her made it all the more exciting, finally I was getting one over on Molly and I was finally better than her at something.